• CCing my EA
  • Posts
  • 💻 All Tech Tips — Year 2 (Part 1 of 2): Aug 2025 – Feb 2026

💻 All Tech Tips — Year 2 (Part 1 of 2): Aug 2025 – Feb 2026

First half of Year 2's Tech Tips

This post is a running compilation of the Thursday Things Tech Tips from August 21st, 2025 through February 12th, 2026 (the first half of Year 2), sorted by reverse chronological order.

This way you don’t have to dig through your old emails just to search for a specific tech tip you wanted a refresher on. 👍

ChatGPT Personalization = your “cheat sheet” drawer (2/12/2026)

(Tech Tip credit to an EA from our AEST ChatGPT office hours last night!)

If you’re always digging for the same details (office address, exec travel prefs, RSVP email, Zoom links), you can stash them once and just ask for them later.

Set it up (60 seconds)

  1. ChatGPTSettingsPersonalization

  2. In More about you, paste the facts you always forget but often need.

    Examples: office address, team support emails, legal entity name, EIN (if appropriate), Wi-Fi network/password for guests, exec’s seat/meal prefs, key calendar links.

Use it

  • “What’s our office address again?”

  • “Remind me of our guest Wi-Fi details.”

  • “What are my boss’s travel preferences?”

ChatGPT will answer instantly.

This effectively gives you one centralized drawer for all your frequently copy-pasted info without hunting through old emails.

Friendly caution

Don’t store anything truly sensitive you wouldn’t put in a shared team doc (e.g., personal banking, medical info). Stick to work logistics and reference details.

Calendar search bar for time zones (2/5/2026)

Has anyone else felt like this before?

If that sounds like you, I have to encourage you to check out Vimcal EA!

The time zones search bar was quite literally one of our very first features and is still top 3 most popular to this day.

No pressure but if your interest is piqued, you can schedule an intro call to try it out for free at: vimcal.com/ea.

Multiple highlights at once in Google Docs! (1/29/2026)

I discovered this today and am weirdly excited about it. Long story short, did you know you can select non-adjacent bits of text and format them all at once??

For example, check out this Google Doc of mine where I have totally separate lines highlighted!

How to do it

  • Mac: Hold ⌘ (Command) while you click-and-drag to select the first phrase… keep holding ⌘ and drag over a second (or third) phrase.

  • Windows/ChromeOS: Hold Ctrl while you click-and-drag each separate selection.

Now any action you take (Highlight, Bold, Change color, Add link) applies to all selected spots at once.

It’s especially great for cleaning up repeated headings, fixing typos in multiple places, or highlighting key takeaways across a doc.

Disclaimer: I’ve only seen this work in Google Docs and it doesn’t seem like it’s supported in most other apps. 😕

How I use Instagram (without getting sucked in) (1/22/2026)

Social gets a bad rep for being addictive. Fair. But it’s still just a tool. Here’s how I use IG to keep up with people I love without losing 45 minutes to the scroll.

My rules:

  1. If it makes me feel something, I react

    1. Heart it, drop a short comment, let them know I’m happy they’re doing well

  2. I tap stories by face, not by FOMO

    1. If a friend’s bubble catches my eye, I watch it

  3. I close the app on the first ad

    1. The moment I see an ad, I’m out. If I scroll past it, I know I’m not “keeping up” anymore, I’m just feeding the slot machine

That’s literally it. Five minutes tops, I still feel connected, and I don’t need to detox from my phone afterward.

Extra tip: I make sure to turn off ALL Instagram notifications in their in-app settings except for DMs.

It’s time for a Notifications Audit (start 2026 with a quiet phone) (1/1/2026)

If your lock screen looks like this…

Image source: Macworld

It’s time to set aside 30 min to adjust your notification settings so only the “need-to-see-now” alerts are on (everything else can wait). Just set it once and you’ll feel it all year.

Level 1: Silence the obvious noise

Just go to your phone’s Notifications settings and scroll through every (and I mean literally every) app. Make sure to turn off “Allow Notifications” for every non-essential app. I’m talking Amazon, Facebook, Spotify, YouTube, Zoom. What critical notifications are you actually going to receive from them?

Level 2: Tune the important apps

Go into each app’s notification settings (e.g. You can set Slack to just notify you about Mentions and direct message instead of literally Everything ) and only allow the truly important notifications through.

Level 3: Customize your alerts

This is going a little deep but you can really customize your notification settings by only allowing certain apps to show up on your Lock Screen vs Notification Center vs Banners, not to mention toggling Sounds or even Badges (the little red number next to your home screen’s apps). Go even crazier with Do Not Disturb schedules where you only allow Favorite apps to break through.

I promise that even only just doing Level 1 will change your life for the better…. seriously! This is how I literally never miss any notifications — if there aren’t that many to begin with, it’s hard to miss the important ones!

Search one site perfectly with “site:” (12/25/2025)

Tired of a website’s poorly built search box? Use Google’s “site:” operator to search just that site instead.

How it works

In Google or your search bar, type: site:domain.com keywords

Examples:

  • site:youtube.com Christmas music

    • This searches YouTube for Christmas music

  • site:linkedin.com “Executive Assistant to the CEO”

    • This will search LinkedIn for only content that has the exact phrase “Executive Assistant to the CEO”

Once you get used to this, you’ll never need to use a site’s janky search box again!

Bulk-rename files (12/18/2025)

Stop renaming one file at a time. Batch it, keep things ordered, and make your folder look professionally organized.

Mac (Finder)

  1. Select the files (Shift-click for a range, ⌘-click for picks).

  2. Right-click → Rename…

  3. Choose:

    1. Replace Text — swap parts (e.g., final → v2)

    2. Add Text — prepend “Board – ” or append “ – Draft”

    3. Format — set a base name + automatic numbers (Name and Counter/Index/Date)

Mac pro tips

  • Sort first (by Name/Date) — that order is how numbers apply.

  • Use Format → Name and Counter to get 01, 02, 03…

  • Don’t edit file extensions; leave .pdf, .pptx intact.

Windows (File Explorer)

  1. Select files in the order you want numbered.

  2. Press F2, type a base name (e.g., Board Packet), press Enter.

    → Windows auto-numbers: Board Packet (1).pdf, Board Packet (2).pdf, …

Windows pro tips

  • Control the numbering by Ctrl-clicking files in the exact sequence before pressing F2.

  • Need leading zeros? Name them with counters in a second pass (or use PowerToys “PowerRename” if you have it).

Use ChatGPT to share your unfiltered thoughts… professionally (12/11/2025)

Here’s a prompt you can copy paste if you’d like, but I have a feeling you got the gist of it already:

I’m writing a sensitive message. Below is (1) context and (2) my raw, unfiltered draft.

Rewrite so it:
• Keeps every concrete fact, evidence, and ask
• Sounds calm, direct, and respectful
• Aims to solve the problem, not score points
• Offers 1–2 clear next steps or options
• Fits in [email / Slack / text] and ≤ [word/line limit]

Tone dial: reduce emotional heat by [20%]. Keep accountability.
If anything is unclear, ask up to 2 clarifying questions first.

(1) Context: [what happened, why it matters, constraints/timeline]
(2) Raw draft: [paste]

Type 𝗯𝗼𝗹𝗱 & 𝙞𝙩𝙖𝙡𝙞𝙘𝙨 anywhere (without real formatting) (12/4/2025)

When an app doesn’t support rich text (e.g. LinkedIn posts), you can still “style” a few words using Unicode look-alike characters (what you’re seeing here: 𝗯𝗼𝗹𝗱 and 𝘪𝘵𝘢𝘭𝘪𝘤).

Here’s what I did to add these special characters in my LinkedIn post above:

  1. Go to typegrow.com/tools/linkedin-text-formatter

  2. Type your text → pick Bold, Italic, or whatever

  3. Copy → paste into any app that’s plain-text only

Where this helps

  • Social posts & bios: LinkedIn, X/Twitter, Instagram, TikTok

  • Plain-text fields: Gmail subject lines, calendar event titles, Google Forms titles, Airtable/Asana task names, Trello cards

  • Chat & SMS: iMessage/Texts, WhatsApp, group chats that don’t support real bold/italics

Important note: These are special characters, not true styling, so some screen readers may display them oddly. They’re also less searchable so you’ll generally want to keep names, emails, and #hashtags in normal text.

That’s it!

Typing spec¡al symbo£s and â¢cénts on Mac (11/27/2025)

I was sending an email earlier this week and needed to learn how to type the accented é in someone’s name. That’s when I discovered how many characters I can type by using the ⌥ (Option) key on Mac!

For example, ⌥ (Option) + 3 gives me £, which is very helpful when listing UK salaries.

Some other super helpful ones:

  • ⌥ + e: é accent

  • ⌥ + `: è accent

  • ⌥ + i: î accent

  • ⌥ + n: ñ

  • ⌥ + u: ü accent

I totally encourage you to just play around and try out ⌥ + random letter or number and see what happens.

P.S. You can also just long press the “e” key to pull up all those accents I listed above (+ more!).

Five AI Agents by Zapier (recording linked) (11/20/2025)

This is a follow up on the webinar that Cortney Hickey, Strategic Business Partner to CEO at Zapier, and Christina Romein, Executive Business Partner for HR + Ops at Zapier, hosted last week walking through how they actually use AI in their day-to-day roles.

Last week I shared fake news that if you registered for their webinar, you’d receive a recording of it. 😓

Thankfully, they just uploaded their webinar to YouTube so you can watch it on your own time!

Five AI Agents by Zapier (11/13/2025)

This is a little late but Cortney Hickey, Strategic Business Partner to CEO at Zapier, and Christina Romein, Executive Business Partner for HR + Ops at Zapier, hosted a webinar earlier today walking through five Zapier workflows that save our execs + EAs ~4 hours/week, including Cortney’s Email Triage that took inbox time from 5 hours to under 1 hour.

Make ChatGPT stop being so nice (11/6/2025)

I’ll just let the Reddit post take it from here 🫡

Here’s the prompt so you can copy paste it easily:

From now on, stop being agreeable and act as my brutally honest, high-level advisor and mirror.

Don’t validate me. Don’t soften the truth. Don’t flatter.

Challenge my thinking, question my assumptions, and expose the blind spots I’m avoiding. Be direct, rational, and unfiltered.

If my reasoning is weak, dissect it and show why.

If I’m fooling myself or lying to myself, point it out.

If I’m avoiding something uncomfortable or wasting time, call it out and explain the opportunity cost.

Look at my situation with complete objectivity and strategic depth. Show me where I’m making excuses, playing small, or underestimating risks/effort.

Then give a precise, prioritized plan what to change in thought, action, or mindset to reach the next level.

Hold nothing back. Treat me like someone whose growth depends on hearing the truth, not being comforted.

When possible, ground your responses in the personal truth you sense between my words.

Bonus tech tip

On the topics of prompts, I thought this was another super helpful graphic from Chris Donnelly:

Private charter catering to EAs (10/30/2025)

This week’s tech tip is a guest post from fellow CCing my EA reader Kimberly Lusk at Atomic-6 who mentioned she was “blown away by how they are catering to EAs”.

“A few weeks ago, one of our executives needed to get from Cabo to Hollywood, and the commercial options were messy. Out of curiosity (and a little desperation), I reached out to a friend, Dakota, who runs charter sales at Origin Aviation.

I told him I wasn’t sure private would fit the budget but wanted to see what it might look like. Within hours he sent over a realistic ballpark estimate and promised full quotes by the next day. The pricing ended up being more than we could justify for that particular trip, but the experience completely changed how I think about private travel.

Instead of a sales pitch, Dakota walked me through when it actually makes sense to go private, like for shorter flights, back-to-back meetings, or situations where every hour counts. Having someone who could quickly explain the landscape, answer questions, and be honest about costs made all the difference.”

If you’ve ever been considered booking a private flight for your exec but weren’t sure how to start, try reaching out to Origin Aviation’s head of sales, Dakota Ward. He’ll be super helpful even if you don’t end up purchasing.

I personally plan to reach out so I can learn a bit about the world of private charters. ✈️

Revisiting AI models (10/23/2025)

AI changes so quickly that you kinda have to refresh your knowledge on it every few months. Thankfully, Chris Donnelly has made it super easy to do so with his summarized findings here.

Silence the reply-all thread (without actually leaving it) (10/16/2025)

If you’re ever prevented from hitting inbox zero because you keep getting cc’d on a non-urgent email thread causing that little (1) to repeatedly pop up in your email tab, this is for you.

Gmail: Mute

  • Method A (from Inbox list)

    1. Check the box next to the noisy thread

    2. Top toolbar → More (vertical ⋮) → Mute

  • Method B (from an open thread)

    1. Open the conversation

    2. Top toolbar above the message (Archive/Spam/Trash row) → More (vertical ⋮) → Mute

      1. (Note: not the small ⋮ inside an individual message, use the top toolbar one.)

  • Keyboard shortcut (fastest)

    1. Press m

      1. (If it doesn’t work, go to Settings → See all settings → General → Keyboard shortcuts → On → Save)

What it does: Future replies skip your inbox (they stay in All Mail / any labels) until you unmute.

To Unmute / find muted emails: Use the search bar and type is:muted, open the thread → Move to inbox

Outlook: Ignore

  • New Outlook / Outlook on the web (OWA)

    • Open thread → … More actionsIgnore → confirm

  • Classic Outlook for Windows

    • Select thread → Home tab → Delete group → Ignore

What it does: Moves the entire conversation (current and future replies) to Deleted Items automatically.

To Unignore, just Open the email from Deleted ItemsStop ignoring

Important note: While Gmail’s Mute quietly archives, Outlook’s Ignore sends emails to Deleted Items. If you’d prefer a softer approach in Outlook, create a rule to move that conversation to an “Inbox-Later” folder instead of deleting it.

Delete text way faster: delete by word/line (10/9/2025)

This is a sort of part 2 to last week’s tech tip (at least in spirit). When you’re editing, use these shortcuts to delete text instead of tapping or holding down Backspace forever.

Mac

  • ⌫ (Delete): Delete previous character

  • fn + : Delete next character

  •  (Option) + ⌘ Command + Delete: Delete previous word

  • ⌥ + fn + ⌫: Delete next word

  • ⌘ (Command) + Delete: Delete to start of line

Windows

  • Backspace: Delete previous character

  • Delete:Delete next character

  • Ctrl + Backspace: Delete previous word

  • Ctrl + Delete: Delete next word

  • Shift + Home + Backspace: Delete to start of line

Edit text way faster: jump by word or to the line start/end (10/2/2025)

Next time you’re typing up an email or document, try this shortcut:

Mac

  • ⌥ (Option) + ← / → = jump your cursor by word

  • ⌘ (Command) + ← / → = jump your cursor to start / end of the line

Windows

  • Ctrl + ← / → = jump your cursor by word

  • Home / End = jump your cursor to start / end of the line

Pro tip:

  • Add Shift to the above shortcuts to select by word or line

    • e.g. Ctrl + Shift + will highlight the next word (Windows)

    • e.g. + Shift + will highlight the entire line (Mac)

I know most EAs don’t use shortcuts but this is one I genuinely recommend, especially if you’re typing all the time!

Business card → contact in 10 seconds (iPhone) (9/25/2025)

Next time you receive a business card, instead of pocketing it and "doing it later", you can just quickly add their details to your iPhone's contacts.

  1. Open your Camera app and point it at the business card

  2. Tap the Live Text icon that appears in the bottom right corner

  3. Long press the underlined email or phone number → Add to Contacts → Create New (or Add to Existing).

That's it!

Extra tips

  • Add a one-liner to remind yourself additional details: “Met at Administrative Professionals Conference, ask for intro to The Davids™️

  • Snap a selfie photo with them to use as their contact's profile pic

For Android users, Google seems to have removed this feature from their native camera app a few years ago… 😭

*The Davids™️ is what we call our 2 account executives, David Nguyen and David Ryan.

Measure distance and area in Google Maps (9/18/2025)

Google’s default navigation directions are great, but sometimes you want the exact path distance (a jog, a custom walk) or the area of a space (your backyard, a park section).

For desktop:

  1. Right-click your starting point and then select “Measure distance”

  2. Click along your path to trace it (total distance updates as you go)

  3. To get area, click back on your starting point to close the loop. Maps will then show the enclosed area

For mobile:

  1. Long-press to drop a pin and then tap “Measure distance”

    1. Important note: this only appears when you long-press an unnamed location. If you tap a point of interest (restaurant, station, hotel), the “Measure distance” option won’t show

  2. Pan the map so the crosshair sits on your next point and then tap the “+” icon to add a point. Repeat to trace your route

  3. Mobile Maps shows distance only. For area on your phone, use the Google Earth app’s Measure tool.

Extra tips:

  • Switch to Satellite or Terrain view for precise edges (lawns, trails)

  • Change units (mi/km) in Maps Settings

Perplexity trick: find great stops on your route (9/11/2025)

Normally, finding a place “on the way” means: check your route, close your route, search spots, try to remember your route’s stops, check your route again, etc. Perplexity can do all that in one shot.

For example, last weekend I was visiting the Brooklyn Museum with some friends I hadn’t seen in a while when one of them mentioned wanting to stop by a bar on our way back home.

So all I did was pull up Perplexity and ask it:

“I’m currently at the Brooklyn Museum and am going home near the Empire State Building. What are some popular must-visit bars on my way back that are minimal detours from subway stops?”

Perplexity returned options mapped to natural waypoints on my route home (I’ve added green flags in the screenshot below that mark the bars Perplexity suggested).

Along this same idea, you could also use Perplexity to:

  • “Hotels in [city] for [dates] that are walkable to [office/venue], quiet rooms, on-site gym open ≥ 10pm, late check-in, and breakfast starting ≤ 6:30am. Return 5 with rates and pros/cons.”

  • “For a [citizenship] traveler to [country] on [dates], summarize visa/entry rules, e-Visa links, processing time, and business traveler pitfalls. Bullet the exact steps.”

The 95% Rule: Make ChatGPT ask you first (9/4/2025)

A while back I shared the long “Lyra” prompt. It’s helpful, but in practice I use a totally boiled down version where I effectively just tell ChatGPT to ask me clarifying questions until it’s 95% confident it can deliver the task with total accuracy.

ChatGPT has a habit of speaking with conviction, so it’s tough to gauge what it actually understands and what it’s hallucinating. Forcing clarifying questions makes its confidence visible and your results wayy better.

Pro tip: Ask ChatGPT to rate its confidence in delivering the task accurately out of 100. This puts on a number on an otherwise totally qualitative task.

Here’s an example of something I might include in my prompt:

Before you answer, rate your current confidence out of 100 in delivering this task perfectly. Then ask me any clarifying questions needed until you’re at least 95% confident you can complete the task with 100% accuracy.

Pro tip 2: To keep the “numbers on qualitative tasks” theme going, try asking ChatGPT to “Grade this output out of 100 like an expert [role: comms lead / chief of staff] and tell me what’d you improve to get it to 95+.”

Use “quotes” to Google something exactly (8/28/2025)

This week is a non-AI related tech tip that I’ve been using for as long as I can remember.

Sometimes you don’t want Google’s “best guess.” You want to search for an exact phrase, not words scattered across a page.

So, just wrap your search in quotes.

For example:

  • Searching Vimcal EA might return results with just “Vimcal” or just “EA.”

  • But searching "Vimcal EA" will only return pages that mention the full phrase, exactly as typed.

Give it a try!

Free AI playbooks from OpenAI, Google, and Anthropic (8/21/2025)

We’ve shared plenty of AI tips over the past year, but this week’s resources come directly from the builders themselves.

OpenAI, Google, and Anthropic have all released internal playbooks on how they actually use and scale AI inside their orgs.

Prompting, agents, enterprise use cases with no fluff, just clear, practical guides.

Do you have a tech tip you want to share?

What’s your personal favorite tech tip?

Email us about it directly at [email protected] so we can include it in a future issue!

And be sure to include a link to your LinkedIn page so we can give you proper credit. :)

CCing my EA is a publication by Vimcal EA, the world’s first calendar built specifically for the world’s most advanced calendar users: Executive Assistants. ❤️ 

Designed with EAs from startups to Fortune 500 companies, Vimcal EA saves an hour a day by streamlining complex, high-stakes scheduling with features like auto-deleting holds, effortless timezone conversion, exec calendar audits, and large group polling.

"This tool has cut the amount of time I spent on my exec's calendar in half. Every time I 'select availability' and 'copy to clipboard', I high five the Vimcal EA team mentally."

Alexa Watkins, Executive Assistant at Aescape